Chris Brown‘s 2009 arrest for physically assaulting then-girlfriend Rihanna was just the beginning of his ongoing legal issues.

Brown rose to stardom after releasing his studio album in 2005. His second album, which was released two years later, featured his hit song “Kiss Kiss,” which put Brown on the path to being the “King of R&B” of his generation.

In 2009, however, Brown made headlines when he was arrested for physically assaulting his then-girlfriend Rihanna. He pleaded guilty to the felony charge and served five years of probation, in addition to community service and domestic violence counseling. Brown and Rihanna briefly reconciled in 2012 before calling it quits again one year later.

“It’s in the past, and I don’t want to say, ‘Get over it,’ because it’s a very serious thing that is still relevant. It’s still real,” Rihanna, who now shares two kids with ASAP Rocky, told Vanity Fair in 2015. “A lot of women, a lot of young girls, are still going through it. A lot of young boys, too. It’s not a subject to sweep under the rug, so I can’t just dismiss it like it wasn’t anything, or I don’t take it seriously. But, for me, and anyone who’s been a victim of domestic abuse, nobody wants to even remember it.”

Brown addressed the arrest — and the photos of Rihanna’s injuries — in his 2017 documentary, Welcome to My Life, saying, “I look back at that picture and I’m like that’s not me, bro, that’s not me. I hate it to this day. That’s going to haunt me forever.”

Brown has continued to face legal troubles since, including a restraining order filed by his ex Karrueche Tran, multiple claims of sexual assault from several woman that he has denied and more. Scroll down for a timeline of Brown’s legal troubles over the years:

2009

One year after they went public with their relationship, Rihanna called the police after being attacked by Brown. The singer was booked on felony criminal threats charges before posting $50,000 bail and later pleaded guilty. After accepting a plea deal, Brown was ordered to complete community labor, five years probation and domestic violence counseling. A judge also issued a restraining order at the time, but it was relaxed in 2011 after Brown and Rihanna’s respective legal consult requested a “level one” order so the former couple could appear at awards shows together.

Brown and Rihanna briefly reconciled after working on several songs together, but called it quits for good in 2013.

2010

Brown was denied a visa to tour in the U.K. after his arrest.

“We reserve the right to refuse entry to the U.K. to anyone guilty of a serious criminal offense,” the U.K.’s home office said in a statement at the time. “Public safety is one of our primary concerns. Each application to enter the UK is considered on its individual merits.”

2011

While promoting his 2011 album F.A.M.E. (Forgiving All My Enemies), Brown got upset when Good Morning America host Robin Roberts brought up his assault of Rihanna and the relaxed restraining order. ABC News confirmed that after the interview, Brown confronted the segment producer before destroying a dressing room window when he threw a chair through it.

“As always, we ask questions that are relevant and newsworthy, and that’s what we did in this interview,” the network wrote in a statement.

Brown, meanwhile, wrote a since-deleted post via X, which read, “I’m so over people bringing this past s— up!!!” He quickly walked the comment back with a new statement, writing, “All my fans!!! This album is for you and only you!!! I’m so tired of everyone else!! Honestly!! I love team breezy!!”

June 2012

Brown was involved in a brawl with Drake at a New York City nightclub that left eight people injured — including NBA star Tony Parker. Drake was not arrested while Brown’s lawyer claimed Drake was the instigator.

Drake and Brown worked out their issues before they appeared in a skit together at the 2014 ESPY Awards. They later poked fun at the brawl in the music video for Brown’s 2019 song “No Guidance,” which featured Drake.

September 2012

While conducting his community service, Brown tested positive for cannabis and appeared before a judge to determine whether he had violated the terms of his court order. He was given a warning from Los Angeles Superior Court Judge Patricia Schnegg, who referred to him as a “rode model” during the hearing. Brown’s probation officially ended three years later.

January 2013

An altercation between Brown and Frank Ocean over a parking space led to police involvement. The authorities investigated Brown for “battery” after he allegedly punched Ocean and threatened to shoot him, according to an incident report obtained by TMZ at the time. Ocean chose not to press charges.

July 2013

Brown’s probation was revoked after his involvement in an alleged hit-and-run incident. The charges were eventually dropped after a settlement was reached, and Brown served an additional 1,000 hours of community service.

October 2013

Brown was arrested for felony assault and spent 36 hours in jail after he refused to take a picture with a man before subsequently breaking the individual’s nose. The charge was reduced to simple assault misdemeanor and Brown was released without bail and ordered to stay at least 100 yards away from the man he was accused of assaulting.

Brown later pleaded guilty to the assault and admitted to misdemeanor assault and was sentenced to time served. He spent two days in a District of Columbia jail after speaking out at the hearing, during which Brown said, “I would like to say to the court that I’m sorry.”

The musician’s attorneys ultimately released a statement on his behalf. “We are pleased with the outcome of today’s court proceedings,” read their statement. “Mr. Brown’s guilty plea finally puts to rest a case that has been pending for almost a year. Today’s result will allow Mr. Brown to focus his attention back on his music and his career.”

March 2014

Shortly after his 2013 arrest, Brown voluntarily entered a rehab facility before he was ultimately kicked out for violent behavior. Brown’s probation officer claimed Brown smashed his own mother’s car window during a family session. Brown was sentenced to three months at a live-in anger management rehab facility, where he was diagnosed with bipolar disorder and post-traumatic stress disorder.

Brown was removed from the Malibu treatment facility because he violated the facility’s “internal” rules. The singer was subsequently arrested and sentenced to 131 days in jail for probation violation.

He was released early from jail in June 2014, but remained on probation and was ordered to complete his remaining community service and see a psychiatrist twice a week.

January 2015

Brown’s probation was revoked after he traveled to a nightclub in San Jose, California for a private performance that resulted in gunfire and five people getting shot. One month later, Brown was denied entry into Canada based on his criminal history before he was set to perform two shows.

May 2015

A misdemeanor battery case in Las Vegas named Brown as a suspect after a man claimed he was hit by Brown during an argument over a basketball game at the Palms Casino Resort. The alleged victim declined to press charges and Brown denied any involvement in the incident.

“Chris is currently in Las Vegas as he is performing at Drai’s on [Tuesday] and receiving a key to the Strip that day as well,” Brown’s publicist said in a statement at the time. “He has a suite at the hotel that has a basketball court and invited friends to come play. An unruly individual showed up uninvited and was removed from the premises. Chris was not in an altercation with this person.”

January 2016

Brown was investigated by police in Las Vegas after Liziane Gutierrez claimed she was “punched in the face” by the singer during a party. She filed a report at the time of the alleged incident, but the Las Vegas police department decided not to press charges.

Gutierrez claimed in Investigation Discovery‘s documentary about Brown in 2024 that she was offered a settlement.

“Chris Brown’s attorney denied these allegations,” read a statement in the doc. “He claims he never laid a hand on Liziane Gutierrez who he said was escorted from the premises after becoming disruptive and out of control and had been previously accused of similar behavior in other instances.”

June 2016

Brown was sued by his manager Michael Guirguis for alleged assault, which was settled out of court three years later.

August 2016

Brown was arrested on suspicion of assault with a deadly weapon after a woman called the police claiming he had allegedly threatened her with a gun. According to the Los Angeles Times, charges were never filed after a nine-hour standoff between the authorities and Brown at his Los Angeles residence.

April 2017

While in Florida, Brown was accused of hitting a club photographer during a paid appearance. The man claimed Brown attacked him, but the performer was not arrested at the time. One year later, Brown was charged for felony battery in relation to the incident. The Tampa Bay Times reported that the charge was dropped in 2019 because of “insufficient evidence to prosecute.”

June 2017

Brown started dating Tran after his split from Rihanna, but the pair briefly called it quits when the singer reconciled with Rihanna in 2012. Brown and Tran later reunited and stayed together until 2014. In 2017, Tran filed for a restraining order against Brown, citing allegations of physical abuse. The order was later extended but Brown denied the allegations at the time.

May 2018

An unidentified woman sued Brown and two other people for sexual battery, battery and assault and intentional infliction of emotional distress after she was allegedly held down and sexually assaulted in the singer’s home. Brown’s legal team denied the claims and police didn’t press any charges due to a lack of evidence. Jane Doe filed a civil suit, which was settled out of court in 2020.

December 2018

Brown was charged with two criminal counts of having a restricted species in the form of a capuchin monkey in his home without a permit. The California Department of Fish and Wildlife removed the monkey from Brown’s house and filed evidence with the LA City Attorney, who then filed charges.

Prosecutors ultimately dropped charges against Brown after he agreed to forfeit his rights to the animal and pay $35,000 for the monkey’s care, according to AP News.

2019

Brown was accused by another woman of aggravated rape, which caused him to be detained in Paris. He denied the claims and then sued her for defamation after the probe was dropped.

April 2021

Brown’s former housekeeper filed a lawsuit after his Caucasian shepherd allegedly attacked her sister at his Los Angeles home. According to the lawsuit, the victim’s injuries required multiple days in the hospital and two surgeries.

A judge later pushed the trial back to September 2023 after the victim had not yet undergone medical examinations related to the injuries. Brown’s former housekeeper accused him of failing to show up for deposition in paperwork filed in September 2024, according to The Blast. She demanded the court provide a date for a hearing to address several loopholes in the case.

June 2021

The Los Angeles police responded to a call from a woman at Brown’s home who claimed a man struck her in the back of the head. Multiple outlets identified Brown as the suspect, but he was not at his home when the authorities arrived.

October 2021

Brown was sued by a U.K. music label who accused him of stealing parts of Red Rat’s 1997 track “Tight Up Skirt” for his 2017 song “Privacy.” Brown subsequently reached a settlement with the company. He was also previously sued for similar claims that he stole aspects of other artists’ music for use in his songs “Pills and Automobiles” and his duet with Drake, “No Guidance.” Those cases were later dismissed.

2022

A Jane Doe filed a $20 million lawsuit against Brown alleging that he drugged and raped her. She recalled attending a party on a boat where Brown allegedly offered her several drinks. The Jane Doe claimed she started to feel strange, so they went somewhere more private on the boat where she alleged Brown proceeded to rape her.

Attorney Ariel Mitchell initially took on the case, but subsequently dropped it after Miami Beach police shared months of text messages between Brown and Jane Doe after the incident. The victim, for her part, maintained that the sexual assault happened and she continued to keep in contact with Brown because she struggled to come to terms with what happened. Brown denied any wrongdoing and a judge dismissed the case in 2022.

Brown responded to the claims via Instagram Stories in January 2022, writing, “I HOPE Y’ALL SEE THIS PATTERN OF whenever I’m releasing music or projects ‘THEY’ try to pull some real bulls—.”

The alleged victim spoke out in Investigation Discovery‘s October 2024 tell-all about Brown, saying, “Chris Brown raped me. I can say that and I know it for a fact instead of telling myself it wasn’t. … Most girls would be happy to have sex with Chris Brown. I didn’t want that. This is not what I wanted.”

October 2023

A lawsuit accused Brown of allegedly beating up Abe Diaw at a London nightclub. According to the lawsuit, Brown was “beating” Diaw in the head with “crushing blows” and knocked him unconscious. Brown then allegedly “continued to ruthlessly stomp” on him for “30 seconds.”

Diaw, allegedly “ended up in the hospital with lacerations on his head and torn ligaments in his leg” and the incident left him with “permanent” damage and “severe emotional distress.”

Brown’s reps did not publicly respond to the lawsuit at the time of the filing.

July 2024

Us Weekly confirmed in July that Brown and members of his entourage were sued for $50 million amid claims of a “violent assault” against four concertgoers. The lawsuit included a temporary restraining order against Brown on behalf of the four concertgoers — Larry Parker, Joseph Lewis, Charles Bush and Damarcus Powell — who were seeking $50 million in compensation for damages. Brown’s legal team denied the allegations at the time.

The plaintiffs were awarded a temporary restraining order from Brown and the other named defendants. The cast has not yet proceeded to trial.

That same month, a staff member and head of back security at Dickies Arena named Frederick R. Overpeck sued Brown over the same incident for $15 million. Overpeck claimed he tried to protect the four men who were allegedly assaulted and as a result sustained severe injuries that prevented him from returning to work.

A Dallas attorney representing Brown released a statement in August 2024 about how his client “never initiated physical contact with anyone.” Lawyer Levi McCathern II claimed the alleged victims approached Brown with “a clear agenda.”

“They were seeking trouble and are directly responsible for the situation that ensued,” McCathern stated. “Chris was unjustly targeted in this incident. These individuals saw him as an opportunity for financial gain and should never have been permitted backstage in the first place. The whole episode was clearly a set up.”

If you or someone you know are experiencing domestic violence, please call the National Domestic Violence Hotline at 1-800-799-7233 for confidential support.

If you or someone you know have been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673).

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